Our First Time
by thinker4567
Summary: The Cup brothers share their first night together.


It was early evening, Elder Kettle had gone out drinking with the Tipsy Troop, something about them being old friends or something. It didn't really matter to the brothers because tonight was their night. With Elder Kettle gone until who knew when they'd decided that tonight would be their first time expieriencing sexual pleasure. Being so close to one another they never really had time to explore masturbation since the other was always sure to be nearby. Tonight though was their time.

At the moment thought they were just spending a nice evening together. They had ordered in a pizza and at the moment were watching the end of Frozen. Mugman was a huge fan of animation, and Cuphead couldn't say no to a good Disney flick. At the moment the smaller cup was in tears, sniffling loudly drawing the attention of his older brother. Mugman with his slimmer frame was currently laying on the couch in front of Cuphead, one of Cuphead's arms around him as the other leaned on a pillow and snuggled Mugman close. Cuphead gently pressed his head forward taking a few deep breaths of his brother's sweet scent as he rested the bottom on his cup on his brother's shoulder.

"Whatcha crying about Mugs?"

"It's just... they remind me of us. I mean loving each other so much and." He sniffled and Cuphead chuckled.

"Crybaby."

At that Mugman glared at his brother. His glare softened though as Cuphead lifted his arm from where it was wrapped around Mugman's middle and gently began wiping the tears from his face. "M'gonna save this for when it rains again."

"Cuppy stop saying that! I'm not a sippy cup anymore!" said Mugman pouting slightly only to laugh as Cuphead began pressing kisses under his eyes. "Cuphead!"

"It's making you laugh." said Cuphead with a grin. "And you know what else will?"

"Cuphead... Cuphead no. Cup... Pfffft!" Mugman burst into laughter as Cuphead slid his fingers under Mugman's blue shirt and began tickling his brother's soft, pale skin. Immediately Mugman's body wracked with tremors as he laughed loudly, sqirming and floundering in his brother's grip. "Stop! Stop!" And with that he lifted his foot and kicked back.

"Ooof!" Cuphead yelped as he was kicked in the balls. Mugman turned and grinned at his brother.

"Who's got the advantage NOW brother?" He laughed as he sat up. Cuphead glared at his brother, but then smiled as Mugman leaned forward and kissed Cuphead. Cuphead smiled and wrapped his arms around Mugman's frame, deepening the kiss.

With no one watching them Cuphead decided to be a bit risky and stick his tongue into his brother's mouth. Mugman's eyes widened at that and a surprised grunt came from him as the muscle invaded his mouth. Mugman had never french kissed someone and gently pressed his tongue against Cuphead's trying to force his own tongue in the other's mouth. As they kissed Cuphead realized his brother had a flavor. It was probably from the variety of drinks that were kept in their cups seeping into their very being. Mugman tasted like chocolate and coffee, an intoxicating and arrousing flavor. Mugman liked warm drinks in his cup and his personaly favorites were hot chocolate with whipped cream and toppings, and coffee flavored with tons of pumps of chocolates, caramels, and hazlenuts.

On the otherhand Mugman was tasting something completely different. While Cuphead was a teenager now he was still a kid when it came to flavors. Cuphead usually filled his own head with fruit juices, punches, and ciders. He tasted of sweet apple and grape and the mixed flavor of fruit punch with the sourness of grapefruit and orange. He jolted suddenly when Cuphead's tongue roughly pressed against the roof of his mouth. Cuphead furiously began rubbing his tongue against the top of Mugman's mouth brushing against the sensitive groves. He tried to pull away but Cuphead's arms wrapped around him holding him in place. A moment later Cuphead pulled back. Cuphead's cheeks were bright red as he looked at Mugman. Mugman gasped for breath, cheeks rosy. He fornwed noticing a strand of spit connecting the two. Cuphead grinned and slurped it up.

"That's so GROSS!"

"Hey!" Cuphead laughed as he was shoved off the couch. He looked up with a huge grin at Mugman who simply sighed and shook his head.

"So... you ready?" At that Mugman stiffened looking down at his brother.

"Uhm yeah... should we just?"

"Bedroom." said Cuphead. "I want this to be nice. Want me to carry you?" He laughed as Mugman smacked him playfully.

"I can walk."

The two cups headed into their bedroom. It was somewhat strange. Cuphead will filled with excitement and it completely radiated off him. Mugman on the otherhand radiated insecurity and shyness as he followed after his brother. The two soon came to their room. Cuphead waited for Mugman to come in, then threw the other onto his bed.

"Wha... Cu Mrggh!" Mugman grunted as Cuphead pressed his lips to Mugman's. Mugman relaxed and closed his eyes, allowing Cuphead control since his brother always seemed more comfortable with that. When CUphead broke the kiss to take a breath Mugman looked up at him.

"Why my bed?"

"Cause mine's all messy and gross. You wanna do it for the first time in that?"

"Do... what?" Mugman asked. "I mean I know we're having sex but, what are we supposed to do?"

"Oh! I asked the guys at school! They said that we should start by getting outselves excited. They said touching each other was a great way to do that. So right now I think we need to take our shirts off."

"Uhm... alright." said Mugman as he pulled himself into a sit up position. He gently began to pull off his shirt while Cuphead ripped his off. CUphead was always a bit more open with his body. He threw his off and looked to Mugman excitedly. Mugman had his shirt half off revealing his slightly tubby middle. Cuphead looked at the adorable belly in front of him and couldn't help himself. He reached his hands out and gently pressed his hands against Mugman's belly.

"EEEYAH!" Mugman squealed as he ripped off his shirt to glare at his older brother. "CUphead!"

"I'm sorry! You're just so cute!" said Cuphead with a grin. Mugman's body was so much different than his own! It was rounder and softer and it felt amazing under his hands. Mugman shivered at the feeling of Cuphead's warm hands against his cold body. He felt slightly ashamed with how chubby he was compared to his brother's slim figure. However Cuphead suddenly leaned forward and began to kiss Mugman's skin. Mugman jumped slightly at that.

"Cu.. Cuphead. Stop, I'm so..."

"Fucking beautiful." Cuphead interrupted, kissing Mugman's belly some more. "You're gorgeous Mugs."

"But I..."

"Your warm and snuggly and... I just want more!" Mugman yelped as Cuphead tackled him, pinning him down to the bed. He continued pressing kisses into Mugman's tummy. Mugman relaxed, the shivered when CUphead stuck his tongue into his belly button and began exploring.

"Bwah! Cuppy that feels... so weird." said Mugman. Cuphead grinned at that and his hands began trailing upwards.

"This feel good Mugs?"

"Yeah but it's nothing really... Agh!" He threw his head back and cried out as Cuphead's tongue gently flicked against his nipple. Immediately Cuphead jolted up and looked at him worry. "I'm okay." Mugman assured him. "I just... it surprised me."

"Did it feel good?"

Mugman thought for a moment. "I think it did. I'm not..." And with that he yelped again, as Cuphead now pinched the bud, teasing it with his fingers. "Cupheaaad."

Cuphead grinned at that, "Oh I think that feels really good don't it Mugs?" He asked as he pinched the nipple more. His other hand went to the other nipple and immediately Mugman let out a deep moan throwing his head back. Cuphead continued to play with Mugman's nipples, first giving them pinches and then giving them little flicks. They soon seemed warm and tender to the touch. Mugman seemed to be writhing under Cuphead's fingers, looking up at his brother with lust filled lidded eyes. He suddenly screamed, grabbing his brother's head as Cuphead leaned down and began licking the nipple furiously with his tongue. Cuphead smiled as he continued his teasing making sure to give the bud plenty of loving. He moved to the other nipple and instead of trying to push his brother's head back Mugman simply grabbed the sheets gripping them as tightly as he could while his brother gave his sore nipples his full attention. Mugman could feel his lower body beginning to respond. He suddenly thrust his hips up and grinded his beginning hard on against Cuphead's pelvis. Cuphead cried out in surprise and fell onto his brother earning a squeal from the other.

"Mugman... You're already hard?" Cuphead asked in surprise. Mugman looked up at Cupehead and blushed softly, nodding his head.

"Are you?"

Cupead blushed, "A... A little. But uh... I'm not all the way yet." Mugman frowned and tilted his head. CUphead's eyes then lit up, "But I know exactly how you can help me with that!"

Mugman looked surprised, "I... I can?" he asked tilting his head.

Cuphead nodded and began easing his pants off. Mugman watched as his brother gently began to shimmy off his signature red shorts. The beginning of a tent was forming in his underpants which were quickly shimmied off too. Immediately Mugman's eyes widened seeing his brother's dick... well anyone's dick other than his own for the first time in person.

"Golly Cuppy."

"What?" Cuphead asked clearly not having noticed Mugman's range of emotions looking at his cock.

"It's so big." Mugman said in amazement feeling ashamed of his own smaller penis. "So, what am I doing?"

"Well uhm. They said you're supposed to jerk me off."

"What?"

"Masturbate me."

"Oh... uhm..." Mugman seemed unsure as he reached for his brother's cock. His fingers gently wrapped around the semi hard mass. Cuphead flinched at that.

"Not so tight."

"Ah, sorry," apologized Mugman as he thought of what he liked doing with his own cock. However curiosity was getting at him first as he explored Cuphead's penis. He ran his palm over the warm skin. He began with small, little jerks and froze when Cuphead moaned. He looked up in worry, but then saw the most content expression on his brother's face.

"Do, do you like this Cuphead?" he asked, giving it a firm pump. Immediately Cuphead tried to cross his legs. Mugman grinned at that. "I'm guessing you do."

"Quit, quit teasing me Mugs." He breathed, glaring slightly at his brother. Mugman laughed at that and began giving firmer, harder pumps. Cuphead grabbed the sheets like his brother had earlier, closing his eyes as Mugman began pumping in a solid rhythm. Soon he had become incredibly hard. Mugman could feel the veins on his brother's cock pulsing with pleasure, and the slight pre cum that had begun to form was making his glove slide about leaving Cuphead to make some of the most enticing noises Mugman had ever heard.

"Hey Mugs, can we try something different?" Cuphead asked, covered in sweat and out of breath.

"Huh? You want me to stop?"

"No... just, can you put it in your mouth?"

"WHAT!?" Mugman shrieked, sitting up and looking indignant at his brother. "I'm not putting that in my mouth!"

"Aww come on!" begged Cuphead. "They guys say it's amazing! And you know I showered earlier and I haven't gone all night. It's as clean as it's ever going to be."

Mugman frowned at that. "Uhm, are you sure that's what the guys said Cuphead?"

"Please Mugs." He gave his best puppy eyes and Mugman sighed softly. He looked nervously at the cock now presented to him. It stood straight and tall, glistening in the slight amount of light in the room and dripping with pre cum. Mugman swallowed as he leaned forward and gently gave the cock a lick. The slight wet warmth made Cuphead jolt, smacking Mugman in the mouth with his dick.

Mugman immediately backed up, scrunching his face. He now had a trail of precum on his cheek. He looked to Cuphead as he gently wiped the cum off with one finger, then placed it into his mouth. It was pretty salty, but other than that it wasn't terrible and it certainly wasn't delicious. His shyness faded as he gave the head a few more licks, twisting his tongue around the head. Immediately Cuphead let out a loud moan and Mugman looked up to see Cuphead's eyes scrunched as he gripped the covers tighter. Mugman smirked, then opened his mouth and took the head in his mouth. It was almost like sucking one one of the giant striped lollipops they got from Baroness von Bon Bon. Just really, really salty.

Cuphead was doing his hardest not to buck into his brother's mouth. It was Mugman's first time and as much as Cuphead was enjoying it he didn't want to rush his brother. His dick currently in his brother's mouth being sucked on with warmth, licks, and slurps. It was, well it was pretty orgasmic. He squeezed his eyes shut tight and shook his legs as the pleasure grew and grew. Mugman's tongue suddenly slipped into Cuphead's slit. Cuphead shrieked at that startling Mugman making him let go with a pop.

"Cuppy!?" Mugman asked worriedly. "Are you?"

"No, no!" said CUphead. "Keep going, please, please keep going!" he begged. Mugman had never seen his brother like this. He felt himself beginning to grow harder and harder. His brother had focused on him first and he had to focus on his brother now. He ignored his own desires and pulled more of Cuphead into his mouth. Immediately Cuphead let out the loudest moan he had ever done, forgetting what he thought earlier and jamming his cock as much as he could into Mugman's mouth. Mugman gagged slightly at that, then tried to remind himself of lollipops. His throat relaxed and he began breathing his nose. He sucked and slurped. Cuphead's words became garbles of pleasure. He felt a coil burning in his bell as he was sucked.

Mugman began to get off to the sounds of his brother's pleasure and reached into his pants and grabbed his own swollen, weeping cock. He began pumping it frantically, becoming desperate for a release. Suddenly Cuphead screamed throwing his head back and Mugman's mouth filled with the liquid from earlier. Feeling himself filling his own cock he released it's load spraying all over his chest. Saltiness filled his mouth and he gagged loudly choking on the white liquid. He coughed furiously, dribbles of white running down his chin and all down his chest. A gentle, warm hand rested on his shoulder and he looked up to see Cuphead looking at him worriedly.

"I'm alright." said Mugman weakly. Just caught me off guard is all. Golly, you sure had a lot of that stuff in you huh?"

"I couldn't help it." said CUphead, blushing. "I've never... it was just like an explosion."

"Did it feel good?"

Cuphead thought a moment. "Yeah, it really did."

"I'm glad." said Mugman smiling. Gently Cuphead leaned forward and kissed Mugman on the lips. However seconds later he shot back wrinkling his little red nose.

"Ugh! Mugs how the hell did you handle that taste!? It tastes AWFUL!" He licked his lips a few times trying to get the taste of his tongue.

"S'all right." said Mugman with a shrug.

"Okay... so now..." Cuphead said, pulling Mugman onto the bed and forcing him to lay on his belly.

"Cuppy?"

"The guys say I have to prepare you."

"Prepare me for..." With that a sharp screech left Mugman. Cuphead had heard he was supposed to shove a finger into Mugman's ass to sort of loosen it up. However he'd barely stuck his finger in before Mugman screeched. "WHAT THE FUCK!" Mugman screamed, spinning and shoving Cuphead off himself. "That HURT!"

Cuphead immediately put his hands up. "Sorry! Sorry! The guys said I was supposed to do that! But you're really, really dry." he said with a frown. "The guys said you had to be wet for this to feel nice." He frowned, "They said you should be really wet after that."

"Well I'm not!" Mugman huffed. "Maybe that's a girl thing! I mean you didn't ask how to have sex with a guy did you?"

Cuphead stared at that with widened eyes, then blushed heavily. "Uhm... no." He laughed nervously. "I just sorta assumed. Uh." He looked around the room. "Let's see, maybe we can use something to make you wet! Uhmmm. Oh!" With that he took a bottle from side table. "We can use this!"

"Cuphead no! That's the lotion Elder Kettle got me!"

"Well yeah but you never use it do you?"

Mugman faltered. "Uhm, well no but I might someday." he finished lamely.

"Well that day is today!" said Cuphead as he squirted a good amount of the liquid onto his hands. "Alright so now I squirt it right in..."

With the Mugman shrieked once more. "CUPHEAD!"

"What!?"

"It's COLD!" Mugman whimpered. He began rolling his hips unsure how he felt about the liquid currently in his butthole. It felt strange, not unpleasant but just strange.

"Well I'll warm it up!" Cuphead said with a smile trying once again. Mugman tensed slightly as he felt his brother's finger circling around his entrance once, twice, three times, and then gently begin to make its way in. Mugman tensed more, breathing heavily and closing his eyes. "Just relax Mugs okay? I won't hurt ya. I promise. You can trust me."

"I know I can it just feels so weird." said Mugman as he took a deep breath and forced himself to relax. He could hear the squelching of the lotion and he could feel a bit of it escaping his entrace as Cuphead forced his finger deeper. It didn't hurt, just felt weird. He wiggled his hips as Cuphead slowly inched his finger inside until it was fully in. He brother then hooked his finger and a groan left Mugman.

"How's it feel?"

"Alright." said Mugman with a shrug. He then let out a loud grunt as CUphead added another finger. "How many are supposed to fit in there?"

"Three I think. It's supposed to make it less painful when my penis goes in."

"Your what!?" Mugman yelped. "Cuphead you're fucking huge! There's no way you're going to fit!"

"Yes I am, relax." said Cuphead as he fit in the third finger. Mugman shimmied a bit to make himself comfortable when suddenly his brother spread his fingers. A soft "eeep" left Mugman as his brother did so. "Feeling good yet?"

"Kinda. I..." All of a sudden his entire body shuddered and a loud moan left him.

"Mugs?"

"There, there." said Mugman suddenly. "Right there."

"Here?" Cuphead asked, rubbing against the spot he had earlier. Mugman let out a louder moan as CUphead began to massage his prostate. "Heh, that feel good?"

Mugman could only let out a purrish groan as his response. His eyes were squeezed tight as he shifted about and tried to get the hands in deeper. The pleasure felt amazing as he wiggled his hips and groaned feeling Cuphead's fingers and nails scratch against his prostate. Cuphead pulled his fingers out dripping in goo. "Here, wanna taste?" He offered his finger to Mugman. Mugman's lidded eyes gazed to his fingers and his tongue wrapped around one of the fingers, pulling it into his mouth and giving it a few good sucks. Cuphead's eyes widened at that and he pulled his hand back and stretched his brother's legs. "Alright you ready Mugs?" He took his lotion and spit covered hand and began rubbing it firmly on his dick. It felt amazing, his dick beginning to spurt a little precum.

"Ready for wha...haaa! Hah!" he breathed heavily as Cuphead gently pushed his dick inside of Mugman's entrance. Mugman let out a sharp whine, then began panting furiously.

"Mu..."

"Fucking MOVE!" Mugman yelled, throwing his head back. Cuphead was startled by that, but returned by letting his wild side out. He slammed into his brother hard digging his girth fully into his brother. Mugman screamed loudly at that, tongue lolling out as he looked up at his brother.

"Are you okay?"

"Fine! Fine! Just go!" said Mugman wiggling about. Cuphead grinned and pulled out slightly, then slammed back into his brother. A loud splurt! was heard and the lotion cum mixture began splattering out of Mugman's hole. Mugman moaned loudly at each thrust, shoving his hips forward to meet with his brother.

"Cuuups!" Mugman whimpered, sweating and panting as he looked at his brother. God Cuphead looked so sexy completely focused on pleasuring him. Mugman looked equally beautiful to Cuphead. His brother with his legs wide open, rocking his hips in time to sheath his cock. He was covered in sweat, eyes lidded with lust, and every now and then he'd yell out a garble of words and thrust his hips up bringing Cuphead a wave of pleasure.

"Cuphead! I... I. Hah! Ahhhhhh!" he shrieked loudly and with that his penis erupted spurting all over his chest and his brother's. Cuphead grinned at that, riding his brother out of his orgasm. Mugman breathed heavily looking up at Cuphead. He took a deep breath, legs shaking as his brother continued pounding into him. "Cuphead... Nygh, stop. I'm so, so." And with that he froze. Cuphead threw his head back and screamed loudly, pounding into Mugman's sensitive pussy one last time. This time however something spurted into Mugman making him yelp and grab onto his sheets. His legs quivered and he tensed before going completely still, breathing deeply. With that Cuphead pulled out and then flopped onto his brother, a grin on his face.

"That was fucking amazing." Cuphead said looking to Mugman. "Mugman you're incredibly. That was so hot and sexy." He praised pressing kisses to Mugman's body and lips. Mugman looked at him and smiled happily, leaning down and gently petting his brother's shoulder.

"You too." he said, wrapping his brother in his arms. "No more moving."

"Huh?"

"Stay." said Mugman, closing his eyes sleepily. CUphead grinned and rested on top of his brother listening to his soft heartbeat and rhythmic breathing.


End file.
